55 Winterset DriveChatham, MA 02633MLS Number 22603375

  • Price: $2,390,000
  • Est. Mortgage of $/month
  • 2 Days on Market
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Federal 30-year interest rate: 6.49% last updated on Jul 9, 2026
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  • 4Bedrooms
  • 1.94Acreage
  • 4Bathrooms
  • 1970Year Built
New Seabury Sotheby's International Realty

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New Seabury Sotheby's International Realty
Office: 508.477.8300
12 Mallway
Mashpee, MA 02649
Spectacular four bedroom home set on one of the largest lots in sought-after Great Hill Estates. With deeded rights to Lover's Lake for swimming, kayaking & fishing just a short path away. Located at the end of a quiet cul-de-sac, this home offers true privacy & views of nature at every turn. Dramatic cathedral ceilings, 4 fireplaces, open floor plan & wraparound deck with elevated views of the expansive property all perfect for entertaining and large family gatherings. The 1st floor has two large family rooms w/ soaring ceilings and floor to ceiling fireplaces, kitchen with granite and island open to a dining area, a primary suite with en-suite bath and laundry and a half bath. Upstairs is a second primary suite w/ fireplace and sitting area, an additional bedroom and a full bath. The walkout lower level has a bedroom, full bath, another washer/dryer and leads to a stone patio with fire pit. Close to Chatham Village, bike path and Chatham beaches. Possible subdivision opportunity.

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Driving Directions

Listed by Janet Stuart of Coldwell Banker Realty

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Location Information

  • Directions Old Queen Anne Road to Winterset Drive, house located at the end on the left.

School Information

  • High School DistrictMonomoy

Rooms

  • Bathroom4
  • Bathrooms Total Decimal 3.5
  • Bedrooms4
  • Full Bath3
  • Half Baths1
  • Laundry Features Laundry Room, First Floor
  • Main Level Bathrooms 2
  • Room Bedroom 2 Features Office/Sitting Area, Closet
  • Room Master Bathroom Features Private Full Bath
  • Room Master Bedroom Features Laundry Areas, Closet

Interior

  • Flooring Hardwood, Carpet
  • Interior Features Recessed Lighting

Utilities

  • Cooling Central Air
  • Cooling YN Yes
  • Heating Hot Water
  • Heating YN Yes
  • Sewer Septic Tank
  • Water Source Well

Legal

  • ZoningR60

Other

  • Association Fee $75
  • Association Fee Frequency Annually
  • Association YN Yes
  • Date Listed07/12/2026
  • Special Listing Conditions Standard

Basic Information

  • Lot Features
    • Bike Path
    • Cape Cod Rail Trail
    • Conservation Area
    • Cul-De-Sac
    • House of Worship
    • Major Highway
    • Marina
    • Medical Facility
    • Near Golf Course
    • Public Tennis
    • School
    • Shopping
  • Mls Area Major West Chatham
  • Mls Status Active
  • Parcel Number CHAT M:0011G B:0074 L:H1080
  • Road Frontage DescriptionPaved

Location

  • Address55 Winterset Drive
  • Building Number55
  • CountyBarnstable
  • StateMA
  • StreetWinterset Drive
  • SubdivisionGreat Hills
  • TownChatham
  • Zip02633

Property

  • Acreage1.94

Exterior

  • Fencing Partial
  • RoofAsphalt, Shingle

Property Information

  • Living Area Units Square Feet
  • Lot Size Square Feet 84,506
  • Lot Size Units Acres
  • Property Condition Updated/Remodeled, Actual
  • Square Feet4,066

Tax Information

  • Tax Assessed Value $1,540,900
  • Tax Year 2026
  • Taxes$5,655

Parking

  • Parking Features Basement
  • Parking Spaces14

Basic Information

  • List Price$2,390,000
  • MLS Number22603375
  • Modification Date07/13/2026
  • Property SubTypeSingle Family Residence

Building

  • BasementFinished, Interior Entry, Full
  • Building Area Units Square Feet
  • Construction Materials Shingle Siding
  • Door Features French
  • Fireplace YN Yes
  • Fireplaces Total 4
  • FoundationPoured
  • GarageYes
  • Patio And Porch Features Deck, Patio
  • Property StyleCape Cod, Contemporary
  • Rooms8
  • Year Built1970

Amenities

  • Appliances IncludedGas Water Heater
  • Other AmenitiesBasement, Fireplace, Golf, Tennis

broker reciprocity The data relating to real estate for sale on this site comes from the Broker Reciprocity (BR) of the Cape Cod & Islands Multiple Listing Service, Inc. Summary or thumbnail real estate listings held by brokerage firms other than New Seabury Sotheby's International Realty are marked with the BR Logo and detailed information about them includes the name of the listing broker. Neither the listing broker nor New Seabury Sotheby's International Realty shall be responsible for any typographical errors, misinformation, or misprints and shall be held totally harmless.

This site was last updated July 13, 2026 8:51 AM UTC. All properties are subject to prior sale, changes, or withdrawal.

New Seabury Sotheby's International Realty has chosen to display only certain towns and/or types or styles of properties. This site may not show all listings that are available through the Cape Cod & Islands Multiple Listing Service, Inc.

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